Bert Stern was photography's baddest bad boy. From the 1950s through the '70s he busted conventions, created iconic images, and with groundbreaking conceptual photography for Smirnoff vodka, led the charge in advertising's "Creative Revolution." He possessed an uncanny eye for, and adored, beautiful women—"I fell in love with everything I photographed," he said. They, in turn, made love to his lens. Magazine readers savored his luscious, naturally composed photos of the likes of Audrey Hepburn, Shirley Maclaine, Sophia Loren, Twiggy, Marilyn Monroe, Madonna, and even Grandma Moses. But Stern hid himself behind his camera and later in the haze of his methamphetamine addiction.

A new documentary, Bert Stern: The Original Mad Man which premiered in New York this month and is directed by Shannah Laumeister, uses the now-83-year-old photographer's own words to bring his the mad-boy persona—and those it affected—to the big screen.

Stern's editorial and advertising photography documented the latter half of the 20th century through portraits in Vogue and Life of the era's most illustrious celebrities—some of whom he made illustrious. In the segment of the documentary, for instance, where he talks about his famous poster for Stanley Kurbrick's film adaptation of Lolita—the one where the actress Sue Lyon is wearing lipstick-red, heart-shaped sunglasses while sucking on a red lollipop—he explains how he helped his long-time friend Kubrick bring the film to the public's attention.

To preempt outcries from the Decency League and other watchdogs, the studio wanted Stern to underplay Lolita youthfulness. In fact, the script actually differs from Vladimir Nabokov's original text, making Lolita 16 instead of 12 as she appears in the book. Movie posters are rarely more than mediocre sales tools, but Stern could not abide mediocrity. What's more, he couldn't resist the temptation to be bad. So, while driving Lyon to the photo shoot, Stern recalled that he serendipitously found the sunglasses in Woolworths, bought them, put them on Lyons and instantly had the perfect shot—the studio be damned. It remains the image most associated with the classic film today, and the perfect evocation of a middle-aged man's lust for younger girls.

Stern was also one of a handful of photographers who was given exclusive access to shoot Marilyn Monroe, resulting in a series of nudes now called "The Last Sitting," published in Eros magazine in 1962, the year she died. In the segment of the film about these sessions, Stern remembered her as having a magical force. He talks about taking her into a locked room—just the two of them—and wishing he could "make out" (a term he uses with reference to many of his models). Whether he did or not was unclear, but Monroe decided to undress, allowing Stern to shoot some of her most revealing—and definitive—pictures. He said it "ended up more nude than he meant." If he did nothing else Stern will be remembered for this series of ethereal images of Monroe posing with translucent scarves.

At 13 when she met Stern, Laumeister was a young Marilyn. Her youthful beauty piqued his interest, and she eventually became his muse. Their "secret relationship," as he describes in a segment about their intimacy, has been ongoing for 40 years, of which he photographed her for 20. But seven years ago she decided to "turn the tables": It was time document as much of his life as he'd allow. "This had grown over time and I realized that it had so much to do with his story," she wrote in a recent email. "I figured someone had to record these stories. So one day, I showed up with a camera and Bert said, 'What are you doing?' And I said, 'I'm making a documentary about you.'" The timing was perhaps fortuitous since Stern says on screen that he reached a "dead end" and needed "something to do."

Despite her almost unlimited access, Laumeister, who grew up to be a movie and TV actress turned poet, writer, cinematographer, and director, admits it was a challenge to break through Stern's reluctance to be seen in front of the camera. This was her first documentary, and the process, she wrote, "was like trying to court a wild animal with a camera." Bert is such "a great escape artist. It took everything I ever learned up till then to learn how to deal with him." But she knew she had something special that no one else could have, and what she captured was the beast at bay. Although The New York Times called it an "adoring profile," Stern is presented as a creative genius whose bad behavior with women and drug addictions, as testified to through his own words and many candid interviews with others, add a disturbing shine to the portrait.

The most wrenching was his ex-wife, the dancer Allegra Kent, with whom he had his three children. Calmly and without rancor, she indicts him for his dalliances and questions whether she ever really loved him.

Laumeister found some emotional scenes, like when Stern's talking about Herschel Bramson, the art director who pushed him into a career as an editorial art director and advertising creative—and also was something of a second father. "Bert always said, 'to succeed, you need a great mentor,'" Laumeister says. "His father was not a mentor, but Bramson was. That man changed his life." In fact his father attempted suicide, Stern said, because he was angry that Bert was ever born.

And speaking of fathers, while his two daughters appeared on camera, Laumeister could not convince Stern's own son to give her an interview: "I asked several times." She did, however, get former lovers and wives to speak candidly and critically about their relationships. The most wrenching was his ex-wife, the dancer Allegra Kent, with whom he had his three children. Calmly and without rancor, she indicts him for his dalliances and questions whether she ever really loved him. His younger daughter admitted she was a daddy's girl, while the older daughter detachedly noted that she felt ignored by him because she wasn't as good looking as her sister. How did Stern feel about these comments when he saw the film? "He didn't seem to notice," Laumeister wrote. "He is blind when it comes to love. He took it in stride. He loves the movie."

As an artist, Stern is genius, and his place in the histories of photography, advertising, and graphic design are secure. As a person, however, his motivations never are made clear in the documentary, despite the way it illuminates his difficult relationship with his dad. Laumeister said she did not have preconceptions about where the film should go. "You know people say, 'Well I loved this artist until I got to know him, until I spent time with him,'" she wrote. "We are all different sides to ourselves, right. Well some people say, 'Oh Bert is a womanizer.' Well that's what people said about de Kooning, and all he did is paint woman right. You can say all kinds of things about Bert or anyone else for that matter who is reflected in front of you, we all have our light and our shadow side."

The truth, wrote Laumeister, is "Bert loves women too much. The journey for him through the mystery of women is a lifetime discovery. Anyhow, I just wanted to reveal the truth about an artist with a complex life story, and let people look at the different sides of man's life and his work."

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